Phosphorus oxychloride → Imidazo(1,5-a)pyridine

HRID 1391382Notes

Reaction equation

HRID 1391382 reaction equation
[CH:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)=O.P(Cl)(Cl)(Cl)=O>>[CH:4]1[N:3]=[CH:1][N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12228441N-Pyridin-2-ylmethyl-formamide

Product 1

HCID 274090Imidazo(1,5-a)pyridine

Procedure

To 13.6 g. of 2-formamidomethylpyridine in a round-bottom flask is added 25 ml. of phosphorous oxychloride. Following the exothermic reaction, the reaction mixture is cooled to room temperature, and quenched on crushed ice. The aqueous mixture is treated with sufficient 20% aqueous sodium hydroxide solution to provide a pH of 9-10 , and the liberated product extracted into chloroform (3 × 300 ml.). The extracts are combined, dried over sodium sulfate and concentrated to a light brown oil, 14.0 g.

Workup

  1. customthe exothermic reaction
  2. customquenched
  3. customon crushed ice
  4. additionThe aqueous mixture is treated with sufficient 20% aqueous sodium hydroxide solution
  5. customto provide a pH of 9-10
  6. extractionthe liberated product extracted into chloroform (3 × 300 ml.)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to a light brown oil, 14.0 g

Sources & evidence

ORD record
ord-5ee25ab36d7a47b889d7e868e66a59c5
Source dataset
uspto-grants-1979_02
Patent number
US04141898

Reaction notes

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